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Synlett 2025; 36(15): 2074-2090
DOI: 10.1055/a-2577-1120
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Emerging Trends in Organic Chemistry: A Focus on India

Emerging Trends of Benzotriazole Ring Cleavage (BtRC) in Organic Synthesis

Mangal S. Yadav
,
Vinod K. Tiwari  ∗

V.K.T. gratefully acknowledge Science and Engineering Research Board, New Delhi (Grant No.: CRG/2021/002776) for the financial assistance and Institute of Eminence (IoE)-BHU for incentive grant. M.S.Y. sincerely thanks IoE-BHU for the RJP-PDF.
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This manuscript is dedicated in memory of (Late) Sh. Lalita Tiwari (16-4-1956 to 26-12-2024), loving father of Prof. Vinod K. Tiwari.

Abstract

The distinct structural features of benzotriazole heterocycle facilitates the formation of new bonds and promotes denitrogenation processes for an easy access to physiologically relevant molecules through benzotriazole ring cleavage (BtRC) path. Several important functionalization of benzotriazole precursors have been now well established, notably the cyclization, arylation, alkenylation, alkylation, carbonylation, and the conception of carbon–heteroatom linkages. This account provides a concise overview on recent developments in the ring cleavage of N-thioacylbenzotriazoles, N-acylbenzotriazoles, N-triflylbenzotriazoles, and N-vinylbenzotriazoles under various conditions along with their growing scope in modern organic synthesis.

1 Introduction

2 Ring Cleavage of N-Thioacylbenzotriazoles

3 Ring Cleavage of N-Acylbenzotriazoles

4 Ring Cleavage of N-Trifylbenzotriazoles

5 Ring Cleavage of N-Vinylbenzotriazoles

6 Miscellaneous Ring Cleavage Applications

7 Conclusion and Future Outlook

Keywords

benzotriazole ring cleavage (BtRC) - benzotriazole - denitrogenation - functionalization


Publication History

Received: 04 March 2025

Accepted after revision: 07 April 2025

Accepted Manuscript online:
07 April 2025

Article published online:
21 May 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

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